Nucleophilic Substitution Induced by Electron Transfer at the Bridgehead of Polycyclic Alkanes: Competition between Polar and Radical Pathways

2001 ◽  
Vol 66 (10) ◽  
pp. 3362-3371 ◽  
Author(s):  
William Adcock ◽  
Christopher I. Clark ◽  
Neil A. Trout
Keyword(s):  
Electron Transfer ◽  
Nucleophilic Substitution

scholarly journals An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

RSC Advances ◽  
2014 ◽  
Vol 4 (34) ◽  
pp. 17490-17497 ◽  
Author(s):  
Silvia M. Soria-Castro ◽  
Daniel A. Caminos ◽  
Alicia B. Peñéñory
Keyword(s):  
Electron Transfer ◽  
Microwave Irradiation ◽  
Nucleophilic Substitution ◽  
Transfer Mechanism ◽  
Ring Closure ◽  
Electron Transfer Mechanism ◽  
Thermally Induced ◽  
Intramolecular Ring

Quick reaction by microwave irradiation promotes nucleophilic substitution by thermally induced electron transfer mechanism and allows to synthesize deoxibenzoin and indol heterocycles derivates by inter or intramolecular ring closure.

Nucleophilic Substitution Reactions by Electron Transfer

ChemInform ◽  
2003 ◽  
Vol 34 (17) ◽  
Author(s):  
Roberto A. Rossi ◽  
Adriana B. Pierini ◽  
Alicia B. Penenory
Keyword(s):  
Electron Transfer ◽  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions

scholarly journals Nucleophilic C–H functionalization of arenes: a new logic of organic synthesis

2017 ◽  
Vol 89 (8) ◽  
pp. 1195-1208 ◽  
Author(s):  
Oleg N. Chupakhin ◽  
Valery N. Charushin
Keyword(s):  
Electron Transfer ◽  
Green Chemistry ◽  
Nucleophilic Substitution ◽  
Organic Synthesis ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Metal Free ◽  
Hydride Ion ◽  
Electrochemical Modeling ◽  
Leaving Groups ◽  
Concept Change

AbstractDirect metal-free C–H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the SNH reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C–H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The SNH reactions, as a part of the general C–H functionalization concept, change the logic of organic synthesis. They open new opportunities, avoiding incorporation of good leaving groups or other auxiliaries in an aromatic ring, as a prefunctionalization step, thus providing a better correspondence to the principles of green chemistry.

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